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Cheap flights from Chicago Midway Airport to San José from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 4/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:41 pm - 8:45 am
MDW
-
SJO
14h 04m
1 stop
Frontier Logo
10:00 am - 7:00 am
SJO
-
MDW
20h 00m
2 stops
$373Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
7:41 pm - 8:45 am
MDW
-
SJO
14h 04m
1 stop
Frontier Logo
10:00 am - 7:00 am
SJO
-
MDW
20h 00m
2 stops
$377Frontier
Sun, May 24 - Mon, Jun 1
Frontier Logo
7:41 pm - 8:45 am
MDW
-
SJO
14h 04m
1 stop
Frontier Logo
10:00 am - 7:00 am
SJO
-
MDW
20h 00m
2 stops
$394Frontier
Thu, May 28 - Sun, May 31
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
Multiple Airlines Logo
7:48 pm - 1:00 pm
SJO
-
MDW
16h 12m
2 stops
$412Multiple Airlines
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
$413Southwest
Tue, May 5 - Mon, May 11
Frontier Logo
7:41 pm - 8:45 am
MDW
-
SJO
14h 04m
1 stop
Frontier Logo
10:00 am - 7:00 am
SJO
-
MDW
20h 00m
2 stops
$419Frontier
Sun, May 24 - Sun, May 31
Multiple Airlines Logo
9:42 pm - 3:05 pm
MDW
-
SJO
18h 23m
1 stop
Multiple Airlines Logo
7:45 am - 10:19 pm
SJO
-
MDW
13h 34m
2 stops
$439Multiple Airlines
Mon, Mar 30 - Tue, Apr 7
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
Southwest Logo
9:00 am - 7:00 pm
SJO
-
MDW
9h 00m
1 stop
$447Southwest
Wed, May 6 - Mon, May 11
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$459Southwest
Fri, Apr 10 - Wed, Apr 22
Multiple Airlines Logo
9:51 pm - 10:42 am
MDW
-
SJO
13h 51m
1 stop
Multiple Airlines Logo
12:19 pm - 10:19 pm
SJO
-
MDW
33h 00m
2 stops
$461Multiple Airlines
Mon, Mar 30 - Mon, Apr 6

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
May 5
MDW6:00 amChicago Midway
7h 10m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
May 11
SJO1:10 pmSan José Juan Santamaria Intl
7h 45m
1 stop
MDW9:55 pmChicago Midway
$413
Southwest
May 6
MDW12:15 pmChicago Midway
7h 45m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
May 11
SJO9:00 amSan José Juan Santamaria Intl
9h 00m
1 stop
MDW7:00 pmChicago Midway
$447
Southwest
Apr 10
MDW5:35 amChicago Midway
7h 35m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
Apr 22
SJO1:10 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:05 pmChicago Midway
$459

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Apr 27
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
May 2
SJO1:21 pmSan José Juan Santamaria Intl
8h 07m
1 stop
MDW10:28 pmChicago Midway
$462
Delta
May 6
MDW6:38 pmChicago Midway
18h 17m
2 stops
SJO11:55 amSan José Juan Santamaria Intl
May 12
SJO1:20 pmSan José Juan Santamaria Intl
22h 22m
2 stops
MDW12:42 pmChicago Midway
$467
Delta
Apr 15
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
Apr 23
SJO1:21 pmSan José Juan Santamaria Intl
8h 07m
1 stop
MDW10:28 pmChicago Midway
$495

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 9, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 5/28

7:41 pm-8:45 am

1 stop14h 04m

San José Juan Santamaria Intl

Mon 6/1

10:00 am-7:00 am

2 stops20h 00m

$373

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 5/24

7:41 pm-8:45 am

1 stop14h 04m

San José Juan Santamaria Intl

Mon 6/1

10:00 am-7:00 am

2 stops20h 00m

$377

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 5/28

7:41 pm-8:45 am

1 stop14h 04m

San José Juan Santamaria Intl

Sun 5/31

10:00 am-7:00 am

2 stops20h 00m

$394

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/11

6:30 am-3:05 pm

1 stop9h 35m

San José Juan Santamaria Intl

Tue 4/14

7:48 pm-1:00 pm

2 stops16h 12m

$412
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop7h 10m

San José Juan Santamaria Intl

Mon 5/11

1:10 pm-9:55 pm

1 stop7h 45m

$413

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 5/24

7:41 pm-8:45 am

1 stop14h 04m

San José Juan Santamaria Intl

Sun 5/31

10:00 am-7:00 am

2 stops20h 00m

$419

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 3/30

9:42 pm-3:05 pm

1 stop18h 23m

San José Juan Santamaria Intl

Tue 4/7

7:45 am-10:19 pm

2 stops13h 34m

$439

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/6

12:15 pm-7:00 pm

1 stop7h 45m

San José Juan Santamaria Intl

Mon 5/11

9:00 am-7:00 pm

1 stop9h 00m

$447

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 4/10

5:35 am-12:10 pm

1 stop7h 35m

San José Juan Santamaria Intl

Wed 4/22

1:10 pm-11:05 pm

1 stop8h 55m

$459

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 3/30

9:51 pm-10:42 am

1 stop13h 51m

San José Juan Santamaria Intl

Mon 4/6

12:19 pm-10:19 pm

2 stops33h 00m

$461

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $512. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $695. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $502. Flights at noon are often more expensive with an average ticket price of $664.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

6h 30m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 6h 30m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 30m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,313 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Dominical
San Gerardo de Dota
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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